Premium
Multicomponent Synthesis of Structurally Diverse Imidazoles Featuring Azirines, Amines and Aldehydes
Author(s) -
Rossa Thaís A.,
Fantinel Mariane,
Bortoluzzi Adailton J.,
Sá Marcus M.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800687
Subject(s) - chemistry , regioselectivity , amine gas treating , aldehyde , nucleophile , combinatorial chemistry , nucleophilic addition , organic chemistry , catalysis
A novel and efficient method for the synthesis of structurally diverse imidazoles through a multicomponent reaction involving an azirine, an amine, and an aldehyde is described. The method is simple and environmentally benign, producing multifunctionalized imidazoles in moderate‐to‐good yields and in a regioselective manner, which was demonstrated by NMR experiments and X‐ray analysis. A mechanism is proposed in which the amine participates not only as a reactant, but also as a nucleophilic reaction promoter.